Patents Assigned to Orogil
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Patent number: 5035816Abstract: A process for preparing alkylsalicylate superalkalinized detergent-dispersant lubricating oil additives: (a) by the acid catalyzed neutralization of C.sub.12 -C.sub.30 alkylphenol with alkaline earth base in the presence of an azeotropic solvent for the water of reaction; (b) by the carboxylation of the first product with CO.sub.2 to partially convert the alkylphenate to alkylsalicylate; and (c) by sulfurization-superalkalinization of the product in the presence of sulfur, alkaline earth base, azeotropic solvent and added CO.sub.2.Type: GrantFiled: September 20, 1988Date of Patent: July 30, 1991Assignee: OrogilInventor: Savino Leone
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Patent number: 5030687Abstract: Alkylsalicylate-containing detergent-dispersant additives for lubricating oils are obtained by (a) neutralizing an alkylphenol by means of an alkali metal hydroxide; (b) carboxylation of the product with carbon dioxide for maximum conversion of the initial alkali metal alkylphenate into alkali metal alkylsalicylate; (c) sulfurization-superalkalinization of the product in the presence of an alkaline earth base followed by carbonation of the product with carbon dioxide.Type: GrantFiled: September 20, 1988Date of Patent: July 9, 1991Assignee: OrogilInventor: Savino Leone
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Patent number: 4764295Abstract: Disclosed are detergent-dispersant additives for lubricating oils that are made by contacting an alkylarylsulfonic acid with an alkaline earth base in the presence of an alcohol having a boiling point in excess of 80.degree. C., water, chloride ions and preferably a C.sub.1 -C.sub.4 carboxylic acid. The products may be made more basic by carbonation. The disclosed additives, when not carbonated, have a TBN up to about 40 and, when carbonated, have a TBN of up to about 100.Type: GrantFiled: May 20, 1985Date of Patent: August 16, 1988Assignee: OrogilInventor: Jean-Louis Le Coent
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Patent number: 4751010Abstract: Disclosed are detergent-dispersant additives useful in lubricating oils prepared by neutralizing an alkylphenol sulfonic acid, followed by sulfurizing/over-alkalinizing the salt obtained and then carbonating the resultant salt.Lubricating compositions comprising a lubricating oil and from about 1 to about 30% by weight of the final composition of a detergent-dispersant additive of the invention are also disclosed.Type: GrantFiled: July 7, 1986Date of Patent: June 14, 1988Assignee: OrogilInventors: Savino Leone, Henri Gaessler
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Patent number: 4514313Abstract: High alkalinity sulfurized alkylphenates of alkaline earth metals useful as lubricating oil additives and methods of making them are disclosed. A sulfurized alkylphenol is neutralized with an alkaline-earth base in the presence of an oil, a glycol, and halide ions, the glycol being present in the form of a mixture with an alcohol having a boiling point above 150.degree. C. Alcohol, glycol, water, and sediment are removed from the resultant medium and the medium is then carbonated. After carbonation, alcohol, glycol, water, and sediment are removed.Type: GrantFiled: June 24, 1983Date of Patent: April 30, 1985Assignee: OrogilInventor: Jean-Louis Le Coent
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Patent number: 4470916Abstract: High alkalinity metallic lubricating oil additives and a method of making them are disclosed. A magnesium alkylbenzenesulfonate and a sulfurized calcium alkylphenate are carbonated in the presence of an oil, magnesium oxide, a glycol, and an amine. The glycol, water, and sediment are then removed from the resulting medium.Type: GrantFiled: June 22, 1983Date of Patent: September 11, 1984Assignee: OrogilInventors: Jean-Louis Le Coent, Bernard Demoures
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Patent number: 4464289Abstract: Super-alkalinized lubricating oil additives and a method of making them are disclosed. A magnesium alkylbenzenesulfonate and a sulfurized alkylphenol are carbonated in the presence of an oil, magnesium oxide, a glycol, and an amine. The resulting medium is neutralized and super-alkalinized with lime, and the glycol and sediment are removed.Type: GrantFiled: June 22, 1983Date of Patent: August 7, 1984Assignee: OrogilInventors: Jean-Louis Le Coent, Bernard Demoures
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Patent number: 4412927Abstract: A process is provided for preparing detergent-dispersant compositions of high alkalinity by:1. Carbonation, at a temperature of between about 100.degree. C. and 250.degree. C., with carbon dioxide of a reaction medium comprising a sulfurized alkylphenate of an alkaline-earth metal having a TBN of between about 1 and 170, an alkaline-earth metal alkylbenzene sulfonate having a molecular weight of more than about 300 and a TBN of less than or equal to about 150, an alkaline-earth metal compound, an alkylene glycol, and a dilution oil;2. Removal of the alkylene glycol; and3. Separation of the superalkalinized metallic detergent-dispersant thus obtained.The metallic detergent-dispersant compositions obtained are useful in improving the detergent-dispersant power of lubricating oils.Type: GrantFiled: February 19, 1982Date of Patent: November 1, 1983Assignee: Orogil CorporationInventors: Bernard Demoures, Jean-Louis Le Coent
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Patent number: 4382004Abstract: A method of preparing magnesium alkylphenates comprising:1. preparing a suspension of "active" magnesium oxide in methanol;2. contacting said suspension with a mixture containing(a) an alkylphenol bearing one or more C.sub.6 -C.sub.60 alkyl substituents;(b) a dilution oil;(c) and optionally a heavy alcohol of a boiling point of between 100.degree. and 200.degree. C., the ratio of number of mols of "active" magnesium oxide to number of recurrent phenolic OH units being between about 0.25 and 2; and3. carbonating the resultant medium under pressure with carbon dioxide.The magnesium alkylphenates thus obtained are suitable detergent-dispersant additives for lubricating oils in amounts of between about 1 and 8 percent of the weight of the oils.Type: GrantFiled: August 3, 1981Date of Patent: May 3, 1983Assignee: OrogilInventor: Jean-Pierre Tassara
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Patent number: 4302342Abstract: A process is provided for preparing detergent-dispersant compositions of a TBN of at least about 200, containing at least about 2 percent magnesium, by:(1) sulfurization by sulfur of an alkylphenol in the presence of a magnesium and/or calcium alkylbenzene-sulfonate of a TBN less than or equal to about 150, an alkaline-earth component selected from among lime, mixtures of magnesium oxide and lime, or a magnesium oxide and alkali hydroxide, and an alkylene glycol;(2) optionally precarbonation of the resultant mixture by means of CO.sub.2 ;(3) super-alkalinization and carbonation of the resultant mixture by means of magnesium oxide and possibly lime, CO.sub.2 and alkylene glycol; and(4) removal of the excess alkylene glycol.The detergent-dispersant compositions obtained are useful in the improvement of the detergent-dispersant properties of lubricating oils.Type: GrantFiled: June 19, 1979Date of Patent: November 24, 1981Assignee: OrogilInventors: Bernard Demoures, Jean-Louis Le Coent
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Patent number: 4293431Abstract: A process of preparing metallic detergent-dispersant compositions is provided by:1. Reacting sulfur with an alkylphenol, bearing one or more C.sub.6 -C.sub.60 alkyl substituents, in the presence of a dilution oil, an alkaline-earth metal alkylbenzene sulfonate of a molecular weight of more than about 300 and a TBN of less than or equal to about 150, an alkaline-earth metal compound, optionally an alkaline-metal hydroxide, a base component of metallic detergent-dispersant of a TBN greater than or equal to 200 selected from among superalkalinized sulfurized alkaline-earth metal alkylphenates, alkaline-earth metal alkylbenzene sulfonates, and mixtures of superalkalinized sulfurized alkaline earth metal alkylphenates and alkaline-earth metal alkylbenzene sulfonates, and an alkylene glycol, at a temperature of between 100.degree. C. and 190.degree. C.;2. Carbonating the resultant mixture with carbon dioxide at a temperature of between 100.degree. C. and 200.degree. C., the amount of CO.sub.Type: GrantFiled: June 19, 1979Date of Patent: October 6, 1981Assignee: OrogilInventors: Bernard Demoures, Jean-Louis Le Coent
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Patent number: 4293430Abstract: Metallic dithiophosphates obtained by the sulfurization of a composition containing:(A) from about 100 to 20 percent by weight of a metallic dithiophosphate of the formula: ##STR1## in which R.sub.1 is an alkenyl or unsaturated cycloaliphatic radical, R.sub.2 and R.sub.3 are alkyl radicals, m is equal to the valence of the metal M, and M represents a metal of Groups IIB, IIIB, IVB, or VIII of the Periodic System of the Elements, preferably zinc;(B) from about zero to 80 percent of an R.sub.4 -COOR.sub.5 alkyl ester in which R.sub.4 is an alkenyl radical and R.sub.5 an alkyl radical, by means of 0.5 to 10 percent by weight of sulfur, referred to the composition to be sulfurized.Use as extreme-pressure and anti-wear additives for lubricating oils, in an amount of between about 0.3 and 15 percent of the weight of lubricating oil.Type: GrantFiled: February 29, 1980Date of Patent: October 6, 1981Assignee: OrogilInventor: Georges Rivier
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Patent number: 4288335Abstract: Metallic dithiophosphates of the formula: ##STR1## in which R.sub.1 is an alkyl, alkenyl, cycloaliphatic, aryl, or heterocyclic radical, R.sub.2 and R.sub.3 are alkyl radicals, preferably C.sub.1 -C.sub.4 radicals, and m represents the valence of the metal M, M being a metal of Groups IIB, IIIB, IVB, or VIII of the Periodic System of Elements, preferably zinc. They are obtained by the action of P.sub.2 S.sub.5 on a monoester alcohol of the formula: ##STR2## and then by reaction of a metal oxide, such as zinc oxide, with the dithiophosphoric acid formed. These metallic dithiophosphates are useful as extreme-pressure and anti-wear additives for lubricating oils in amounts of between 0.2 and 10 percent, referred to the weight of lubricating oils.Type: GrantFiled: March 4, 1980Date of Patent: September 8, 1981Assignee: OrogilInventor: Georges Rivier
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Patent number: 4251379Abstract: New detergent-dispersants of high alkalinity useful as additives for lubricating oils and a novel process for their preparation are provided.The novel detergent-dispersant additives are prepared by:(1) sulfurizing an alkylphenol in the presence of an alkylbenzene sulfonate of low or zero T.B.N., an alkaline earth base and an alkylene glycol;(2) precarbonating the mixture thus obtained;(3) super-alkalinizing and carbonating the resultant precarbonated mixture by means of an alkaline earth base, CO.sub.2, and an alkylene glycol; and(4) eliminating the excess alkylene glycol.These detergent-dispersant additives improve the detergent-dispersant power of lubricating oils.Type: GrantFiled: January 26, 1979Date of Patent: February 17, 1981Assignee: OrogilInventors: Jean-Louis Le Coent, Bernard Demoures
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Patent number: 4224171Abstract: Novel lubricant additives containing phosphorus and nitrogen and novel lubricant compositions containing between about 0.2 and 10 percent by weight of said additives are provided. The novel lubricant compositions possess improved wear-resistance and improved properties under extreme pressure.Type: GrantFiled: October 23, 1978Date of Patent: September 23, 1980Assignee: OrogilInventors: Georges Rivier, Gerard Forat
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Patent number: 4199462Abstract: New lubricant additive compositions containing at least one alkenyl succinimide of the formula: ##STR1## in which R is an alkenyl group of C.sub.20 -C.sub.200,m is a whole number from 1 to 3,n is a whole number from 0 to 2, withm+n being from 1 to 3.They are produced from the reaction of an alkenyl succinic anhydride comprising a C.sub.20 -C.sub.200 alkenyl group and at least one amine of the formula: ##STR2## in which x is a whole number from 1 to 3. The additive compositions are useful in lubricating oils.Type: GrantFiled: November 9, 1978Date of Patent: April 22, 1980Assignee: OrogilInventors: Gerard Soula, Jean-Paul Lefevre
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Patent number: 4189389Abstract: New lubricant additive compositions containing at least one alkenyl succinimide of the formula: ##STR1## in which R is an alkenyl group of from about 20 to 200 carbon atoms and m is a whole number from 1 to 3.They are produced from the reaction of an alkenyl succinic anhydride comprising a C.sub.20 -C.sub.200 alkenyl group and tris(5-amino-3-thia-pentyl)amine. The additive compositions are useful in lubricating oils.Type: GrantFiled: January 9, 1979Date of Patent: February 19, 1980Assignee: OrogilInventor: Gerard Soula
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Patent number: 4168242Abstract: Novel compositions of matter comprising alkenyl amines are provided. They are prepared by the reaction of a halogenated polyolefin with at least one polyamine having an ether group, such as tris(6-amino-3-oxa-hexyl)amine, N,N-bis(6-amino-3-oxa-hexyl)ethanol amine, N-ethyl-N,N-bis(6-amino-3-oxa-hexyl)amine, etc.The novel compositions of matter provide detergent-dispersant additives for use in lubricating oils and fuels.Type: GrantFiled: January 27, 1978Date of Patent: September 18, 1979Assignee: OrogilInventor: Gerard Soula
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Patent number: 4094802Abstract: Novel lubricant additives are provided comprising compositions based on alkenylsuccinimides containing at least one alkenylsuccinimide of the formula: ##STR1## WHERE R is an alkenyl group of about C.sub.20 to C.sub.200, m is an integer equal to 0, 1 or 2, and n is an integer equal to 0 or 1. These compositions can be prepared by condensation of an alkenylsuccinic anhydride with N,N,N',N'-tetrakis-(3-aminopropyl)-ethylenediamine.Type: GrantFiled: March 30, 1977Date of Patent: June 13, 1978Assignee: Societe OrogilInventors: Gerard Soula, Philippe Duteurtre
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Patent number: 4081388Abstract: New compositions, based on alkenylsuccinimides, are provided which impart useful dispersing, detergent, anti-rust and anti-foam properties when employed as an additive in a lubricating oil. The new compositions are alkenylsuccinimides obtained by condensing an alkenylsuccinic anhydride with at least one polyamine of the formula: ##STR1## in which formula R'.sub.4 is a -r-O-r' radical, R'.sub.5 is one of the radicals -r-O-r'-NH.sub.2, -r'-NH.sub.2, or -r-OH, R'.sub.6 is one of the radicals -r-O-r-NH.sub.2, -r'-NH.sub.2, -r-OH, C.sub.1 -C.sub.4 -alkyl or phenyl, and r and r' have the definition given fully below using a molar ratio of polyamine to alkenylsuccinic anhydride of less than 1.Type: GrantFiled: April 5, 1976Date of Patent: March 28, 1978Assignee: OrogilInventors: Gerard Soula, Philippe Duteurtre